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Since 2005, Bobson has taught math in New York City public high schools. He is a three-time recipient of the Math for America Master Teacher Fellowship and is also a New York State Master Teacher. He is a member of the Advisory Council of the Museum of Mathematics and the Nominations & Elections Committee of the National Council of Teachers of Mathematics (NCTM).

Bobson has written and spoken extensively on mathematics education. He is the co-author of The Math Teacher's Toolbox: Hundreds of Practical Ideas to Support Your Students (Jossey-Bass, 2020). He was a panelist for the 2012 PBS television program American Graduate: A Conversation with Teachers, hosted by Ray Suarez. He has published articles in several publications, including NCTM's Mathematics Teacher journal, Education Week, the Washington Post, and Math for America Teacher Voices blog.

Bobson has also worked to improve the quality of education in New York State. In 2015, he served on the New York State Education Department (NYSED)'s Committee for Regents Exam in Geometry (Common Core) Standard Setting. In 2016, he was selected to NYSED’s Common Core Mathematics Standards Review Committee, which reviewed and revised the Common Core standards for the state. He was also a member of the United Federation of Teachers's Common Core Standards Task Force. In 2018, he was a member of NYSED's Evaluation Workgroup to Explore Current New York State Requirements and Best Practices for Teacher and Principal Evaluation. As an Educational Specialist for NYSED, he writes and edits questions for New York State's high school Regents exams for Algebra II.

Bobson graduated from the Bronx High School of Science, Princeton University (B.A., history), the University of Wisconsin-Madison (M.A., history), and St. John's University (M.S.Ed., adolescent education, mathematics), where he received his teacher training in the New York City Teaching Fellows program.

Bobson runs Reach the Source, which contains resources related to Common Core high school math in New York State. His Twitter handle is @bobsonwong.